Month: June 2021

Application of 135908-33-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 135908-33-7 name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture containing methyl 4-aminobicyclo[2.2.2]octane-l-carboxylate (298mg, 1.63 mmol), 4′-tert-butylbiphenyl-2-carboxylic acid (414 mg, 1.63 mmol), DMAP (227 mg, 1.86 mmol) and EDC HCl (470 mg, 2.45 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by chromatography (elution = 16:1 petrolueum ether/EtOAc) to afford methyl 4-(4′-fcrt-butylbiphenyl-2- ylcarboxamido)bicyclo[2.2.2]octane-l -carboxylate as an off-white solid (186 mg, yield: 27%). 1H NMR (400 MHz, CDCl3): delta 7.74 (IH, d, J= 6.4 Hz), 7.48-7.39 (4H, m), 7.35- 7.31 (3H, m), 4.77 (IH, s), 3.62 (3H, s), 1.79-1.75 (6H, m), 1.62-1.58 (6H, m), 1.36 (9H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/100423; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 88709-17-5, The chemical industry reduces the impact on the environment during synthesis 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

Under an atmosphere of nitrogen, n-butyllithium (50 ml, 15% w/w solution in hexane) was added to a solution of diisopropylamine (7.25 g) in tetrahydrofuran (90 ml) at -30 C. The mixture was stirred at -30 C. for 30 minutes, cooled to -75 C., and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 30 ml), was added slowly. A solution of ethyl 2-ethoxy-4-methylbenzoate (10 g) in tetrahydrofuran (10 ml) was then added at -75 C. and the mixture was stirred for two hours. Carbon dioxide gas was then purged into the reaction mixture at -75 C. till complete decolorization. The reaction mixture was then brought to room temperature, diluted with water (100 ml), and extracted with dichloromethane (100 ml). The aqueous layer was acidified with 10% aqueous sulphuric acid to pH 1.95 and extracted with toluene. The combined toluene layer was washed with water and concentrated in vacuo. Crystallisation with ethyl acetate/petroleum ether afforded (3-ethoxy-4-ethoxycarbonyl)-phenyl acetic acid 7.2 g (59.5%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-ethoxy-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banbaxy Laboratories Limited; US6686497; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1459-96-7,Some common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, molecular formula is C12H18O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

At atmospheric conditions, 0.25g of the Ru-TRIPHOS catalyst ruthenium 1 ,1 ,1 -tris(diphenylphosphinomethyl)ethane, 25 mg of p-toluenesulfonic acid, 2.5g of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate and 50 imL of p-xylene were added to a 100 imL autoclave reactor. The reactor was then purged three times by pressurizing with nitrogen to 200 psig, then venting the pressure to atmospheric each time. The reactor was then purged three times by pressurizing with hydrogen to approximately 300 psig, then venting the pressure to atmospheric each time. Agitation at 800 rpm was then commenced, and hydrogen was then added to bring the pressure to 1600 psig. The temperature was then increased to 200 C while allowing pressure to rise. After the temperature reaches 200 C, the hydrogen pressure was increased to 2000 psig. These conditions (200 C and 2000 psig) were held for 24 hours of reaction. After 24 hours of reaction, the agitation was stopped, and the heat turned off to let the autoclave start cooling. After cooling to room temperature, pressure was released, and the contents were purged with nitrogen gas and vented. The solution was finally discharged from the autoclave and analyzed by GC-MS and 1H NMR. The conversion of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate is 30% and the only product methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1 -carboxylate (100% selectivity).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, its application will become more common.

Reference:
Patent; EASTMAN CHEMICAL COMPANY; HU, Yue, Rachel; HEMBRE, Robert, Thomas; TUSTIN, Gerald, Charles; LIU, Zhufang; ADAMS, Steven, J.; CLARKSON, Jasper, Randle; (59 pag.)WO2019/75004; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3044-06-2,Some common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, molecular formula is C11H18O5, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of l-ethyl-lH-pyrazol-5-amine (16 gm, 0.144 moles) (example 2) and 2-(l-ethoxy-ethylidene)-malonic acid diethyl ester (29 gm, 0.12 moles) (example 3) was stirred at 1200C for about 2 hrs. When the reaction was complete on TLC, crude reaction mixture was concentrated in vacuo to remove ethanol, which was formed as byproduct. Crude residue was taken in phosphorous oxychloride (50 ml) and heated at 115 C for about 12-13 hrs. The reaction mixture was poured into ice-cooled water with continuous stirring. Solid which precipitated out was filtered and dried under vacuum to afford title compound as creamy white solid.Yield: 12 gm (57.17%) m/z: (M++l) 268.28

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-(1-ethoxyethylidene)malonate, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; RUDRA, Sonali; GUPTA, Nidhi; CHANDRAKANT, Kakade, Ganesh; JAIN, Tarun; VOLETI, Sreedhara, Rao; RAY, Abhijit; DASTIDAR, Sunanda G.; VIJAYKRISHNAN, Lalitha; WO2010/46791; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 619-42-1 as follows. COA of Formula: C8H7BrO2

Step 1 Synthesis of 4-Phenylamino-benzoic acid methyl ester A mixture of Pd(OAc)2 (5 mg, 0.02 mmol), dicyclohexylphosphino-2′,3′-dimethoxy biphenyl (17 mg, 0.04 mmol) in toluene (20 mL) was purged with argon gas for 10 minutes, To the resulting mixture was added, aniline (136 mg, 1.46 mmol) and K3PO4(136 mg, 1.46 mmol) and purged with argon gas for 10 minutes and to which added 4-bromobenzoicacid methyl ester (300 mg, 1.4 mmol) and heated to reflux overnight. The reaction mixture was diluted with ethyl acetate and filtered the residue; the filtrate collected was concentrated under reduced pressure to afford the crude mass. The resultant mass was purified by column chromatography (using 60-120 silica gel and 10% EtOAc in Hexane as eluent) to afford 201 mg (63.4%) of 4-Phenylamino-benzoic acid methyl ester.

According to the analysis of related databases, 619-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bischoff, Alexander; Subramanya, Hosahalli; Sundaresan, Kumar; Sammeta, Srinivasa Raju; Vaka, Anil Kumar; US2010/160323; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 87-24-1, name is Ethyl 2-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-methylbenzoate

A solution of ethyl 2-toluate (17, 41.2 g, 0.25 mole) in carbon tetrachloride (200 mL) was added dropwise to a stirring mixture of benzoyl peroxide (100 mg), carbon tetrachloride (200 mL), and NBS (44.5 g, 0.25 mole) at 0 C. The mixture was heated at reflux for 3.5 hr under nitrogen, and allowed to cool to room temperature overnight. The precipitated succinimide was removed by filtration and the filter cake was washed with carbon tetrachloride. The combined filtrates were washed successively with 2 N NaOH (100 mL), and water (2*100 mL), and the solution was dried over anhydrous MgSO4, filtered (Celite), and evaporated under vacuum to yield an oil. Drying under high vacuum overnight afforded 60.5 g (99%) of compound 18: 1H NMR of the product showed the presence of ca. 15% of unreacted 17. The mixture was used in the next step without further purification: 1H NMR (CDCl3) delta 1.43 (t, J=7 Hz, 3H, CH2 CH3), 4.41 (q, J=7 Hz, 2H, CH2CH3), 4.96 (s, 1H, CH2Br), 7.24 (m, 1H, ArH), 7.38 (m, 1H, ArH), 7.48 (m, 2H, ArH).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DarPharma, Inc.; US2007/155720; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 55666-43-8, name is tert-Butyl 3-bromopropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: tert-Butyl 3-bromopropanoate

Sodium Hydride (60% dispersion in mineral oil, 10. [1G,] 0.252 mol) was added portionwise to a stirred solution of [2-OXAZOLIDINONE] (20g, 0.23 mol) in dry tetrahydrofuran [(250ML)] at 0 [C] under nitrogen. After stirring for 30 minutes tert-butyl bromoacetate (50.8 [MI,] 0. [344MOL)] was added slowly and the reaction mixture was left heating to room temperature and stirred overnight. Water was then slowly added followed by ethyl acetate [(250ML).] The aqueous phase was extracted and washed with ethyl acetate [(50ML).] The combined organic phases were washed with brine [(200ML),] dried over magnesium sulphate and concentrated under vacuum. The title compound crystallized on standing as a white solid (45g, 97%). ‘H-NMR (400 MHz, [CDC13)] : [8=] 1.46 (s, 9H), 3.68 (t, 2H), 3.91 (s, 2H), 4.36 (t, 2H

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25662-28-6 as follows. Safety of Methyl 1-cyclopentene-1-carboxylate

EXAMPLE 37; N-((lR)-l-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-2- fluoro- 1 -hydroxy cyclopentanecarboxamide; Methyl cyclopent-1-ene-l-carboxylate (30.0 g, 237.8 mmol) was dissolved in 20 mL of dichloromethane and 3-chloroperbenzoic acid (64.4 g, 373.3 mmol) was added. The reaction was allowed to stir vigorously for 2 hours. The reaction mixture was diluted with EtOAc and washed with 0.5 NNuaOEta. The organic layer was dried over sodium sulfate, filtered and concentrated to give 48.0 grams of methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate. Methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate (2.10 g, 14.8 mmol) and N,N-diethyl- ethanamine trihydrofluoride (4.76 g, 29.5 mmol) were heated in a sealable Emrys microwave vessel with stir bar a microwave reactor at 180 0C for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was further washed with water and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude oil, which was subjected to chromatography on silica gel eluting with 0 to 25% EtOAc in hexanes to afford racemic trans methyl^-fluoro-l-hydroxycyclopentanecarboxylate.The racemic trans methyl-2-fluoro-l-hydroxycyclopentanecarboxylate (0.285 g, 1.76 mmol) was dissolved in 21.3 mL of a 4:1 solution of TEtaF:deionized water. A solution of 1 NNaOH was added to the reaction mixture, which was stirred for 1.5 hours. The reaction was acidified with 6 NHCl and extracted with EtOAc three times. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid as a colorless oil.To a mixture of the compound of Reference Example 4 (0.215 g, 6.13 mmol), racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid (90.8 mg, 0.61 mmol), and (lH-l,2,3-benzotriazol- l-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (0.380 g, 0.86 mmol) in 3 mL of dichloromethane was added triethylamine (0.155 g, 1.53 mmol). This reaction mixture was allowed to stir at ambient temperature for 1 hour. The reaction mixture was washed with water, 0.25 NEtaC1, and EPO saturated aqueous sodium bicarbonate solution prior to drying over sodium sulfate. Filtration and solvent removal provided material which was subjected to chromatography on silica gel eluting with 0-40% EtOAc in hexanes to give a mixture of the two diastereomers. Subsequent preparatory TLC eluting with 40% EtOAc in hexanes yielded the title compound. Less polar diastereomer (beige solid): mass ion (ES+) of 481.0 for M+H+: 1H NMR (500 MHz, CDCI3) delta 8.11 (s, IH), 7.66 (bs, NH), 7.35 (d, J= 2.0Hz, IH)5 7.34-7.25 (m, 2H), 5.48 (quint, J= 6.8 Hz, IH), 4.71 (dd, J= 3.9 Hz, J= 53.0 Hz, IH), 4.33 (s, 3H), 4.20 (s, OH), 2.19-2.16 (m, 2H), 1.99-1.92 (m, 4H), 1.467 (d, J= 6.8 Hz, 3H). More polar diastereomer: mass ion (ES+) of 481.0 for M+H+-‘ 1H NMR (500 MHz, CDCI3) delta 8.13 (s, IH), 7.483 (bs,NH), 7.35 (d, J= 9.0 Hz, IH), 7.28-7.24 (m, 2H), 5.47 (m, IH), 4.79 (dd, J= 3.4 Hz, J= 53.0 Hz, IH), 4.34 (s, 3H), 4.23 (s, OH), 2.26-1.91 (m, 6H), 1.46 (d, J= 6.6 Hz, 3H).

According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/132837; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 685892-23-3, category: esters-buliding-blocks

Step 1. Preparation of methyl 2-chloro-6-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)benzoate (i-5a) [00144] To a solution of methyl 2-bromo-6-chlorobenzoate (7.50 g, 30.1 mmol) in dioxane (65 mL) was added Bis(pinacolato)diboron (15.3 g, 60.3 mmol), AcOK (3.54 g, 36.1 mmol) and PdCl2(dppf) (0.66 g, 0.90 mmol) under N2 atmosphere, then the resulting mixture was stirred at 100 C for 18 h, cooled to room temperature, filtered and concentrated, the residue was purified by chromatography (0-3% EtOAc in petroleum ether) to give the title compound. MS: 297 (M+l). XH NMR (400 MHz, CDC13) delta 7.67 (d, J = 7.4 Hz, 1H), 7.46 (d, J = 7.8 Hz, 1H), 7.29-7.39 (m, 1H), 3.92 (s, 3H), 1.32 (s, 12H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-6-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAPOINTE, Blair, T.; FULLER, Peter, H.; GUNAYDIN, Hakan; LIU, Kun; SCOTT, Mark, E.; TROTTER, B., Wesley; ZHANG, Hongjun; (211 pag.)WO2017/75182; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 57486-69-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 57486-69-8 as follows.

Methyl o-bromophenylacetate (4.6g, 0.02mol),2,6-Dichloroaniline (16.4 g, 0.1 mol),Copper iodide (1.92g, 0.01mol),Anhydrous potassium carbonate (11.2g, 0.08mol) and xylene (100ml) were placed in a dry reaction flask.Under nitrogen protection,The reaction was stirred at 200C for 50 hours under reflux.Activated carbon is added after the reaction is completed.Hot filter,The filtrate was concentrated to dryness under reduced pressure.The residue is dissolved in methanol,Crystallize in ice water bath,Suction filtrationWhite solid 5.50g (diclofenac methyl ester) was dried,Yield 87.8%.

According to the analysis of related databases, 57486-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huazhong University of Science and Technology; Zhu Dajian; Li Tao; Chen Jian; Bi Jiajun; Meng Di; (7 pag.)CN107793323; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics